For years now, Microsoft watchers have wondered about the timing and other specifics of Steve Ballmer’s departure. Now we know them — or a lot more than we did yesterday, anyway. After 33 years at the company, the executive who started at Microsoft in 1980 and has been its CEO since 2000 has announced that he’ll retire within the next 12 months, once a successor has been named.

For folks interested primarily in the stock market, Ballmer’s time as Microsoft’s head honcho is defined by the fact that its shares have largely flat-lined during his tenure. Here, courtesy of Wolfram Alpha, is a chart comparing how MSFT has compared to AAPL during that time period:

Wolfram Alpha

If you — like me — don’t care much about Microsoft’s stock price, Ballmer’s legacy is far more complicated. It can’t be summed up in a chart or a tweet or even in one blog post.

I am not among the man’s harshest critics, in part because I believe that all tech-company hegemonies are destined to decline, sooner or later. The dustbin of tech-company history is littered with outfits which were once market-defining behemoths: Lotus, WordPerfect, Netscape, Palm and oh, so many more. Microsoft in 2013 is not a company on the verge of joining them: It’s still making vast amounts of money and managing to be highly competitive in everything from mundane business software to blockbuster videogames.

Getty Images

Bill Gates and Steve Ballmer pose together upon Ballmer’s appointment as Microsoft CEO in January 2000

Bottom line: I’m pretty sure that there are alternate universes in which the company was run by someone else in recent years — maybe even Bill Gates himself — and fared considerably worse than it has under Ballmer.

Still, I can’t imagine that there’s anyone out there who believes that it’s a given that Microsoft will be anywhere near as important to the future of personal computing as it has been to its the first four decades. Including Steve Ballmer: Last month, he instigated a massive reorg, with the aim of turning Microsoft into a “devices and services” company. Those moves acknowledge that the Microsoft of the future, assuming it’s successful, won’t be the Microsoft we’ve known.

Like the reorg, many of the most notable Microsoft moments of the past few years involve sudden, epoch-shifting change. Ballmer’s company has done things you wouldn’t have expected Microsoft to do, from giving Windows 8 an entirely new primary interface to making its own PC hardware. It’s been a lot for the company’s customers to process all at once, particularly since so many of them value comfortable familiarity over great leaps forward. (Exhibit A: Windows XP, the 12-year-old operating system Microsoft can’t kill.)

If Microsoft is behaving like it’s trying to make up for lost time, it’s because…well, it’s because it needs to make up for lost time. And it’s lagging behind Apple and Google in the race to define the future of personal computing mostly for one simple reason: For too many years, Windows was too damn successful. At some point along the way, Microsoft’s golden goose became an albatross.

The Windows era — which began with Windows 3.0 in 1990 and continues on, at least if you’re talking about laptops and desktops — made billions for Microsoft and its investors. But it also gave the company a number of bad habits it’s still trying to overcome.

Such as:

Windows’ success led to hubris. From its very earliest days, Microsoft was never a company afflicted by a crippling lack of self-confidence. In the years when it was crushing the competition in categories such as PC operating systems and productivity software, being unimaginably headstrong helped. But after that competition was crushed, Microsoft lost its ability to take the most serious threats to its dominance of personal computing seriously. (I’m still not sure whether Ballmer’s famous blustery dismissal of the iPhone was sincere or not — but either way, it was unfortunate.) The company also treated paying customers shabbily in some instances — like with the dismal copy-protection scheme it insultingly named Windows Genuine Advantage — in a way that couldn’t have been less humble or less lovable.

It gave Microsoft tunnel vision. Microsoft has a remarkable track record for identifying important trends early on and diving right in — from pocket-sized computers to tablets to smartwatches. But it nearly always saw them as offshoots of its Windows empire, an outlook which led to misbegotten product-design decisions, such as giving Windows Mobile a microscopic Start button. Only after Apple released the iPhone — a new device that didn’t look or work like a tiny Mac — did Microsoft come around to the notion that new stuff shouldn’t necessarily be very much like old stuff, a philosophy that led to the Metro interface used by Windows 8 and Windows Phone.

It encouraged sloth. Microsoft’s nadir came back in the middle of last decade, when Bill Gates was still involved on a day-to-day basis as Chief Software Architect. That’s when the company released Windows Vista, a product which fixed very few of the many things about Windows that needed fixing. It’s also when it let Internet Explorer 6 calcify into an unusable, archaic wreck. A Microsoft which was running scared would have released much better products on a far faster schedule.

It provided Microsoft with too much money to play with. Microsoft has long been a famously patient company, willing to plug away at markets for years before making much headway or turning a profit. That’s sometimes paid off spectacularly, as in the case of Microsoft Office. But by being able to afford to try almost anything, Microsoft hasn’t had to face the character-building challenge of picking its battles. For instance, as much as I’m glad that Bing exists and provides Google with its only real search-engine competition, it’s hard to figure out how Microsoft has benefited from being in the search business. Mostly, it’s been a money pit and a distraction.

Justin Sullivan / Getty Images News

Ballmer delivering the keynote at Microsoft’s BUILD conference in San Francisco on June 29, 2013

Ballmer, of course, has been partially or entirely responsible for every strategic decision Microsoft has made in this century. So I’m not blaming Microsoft’s woes on Windows’ inordinate success as a way of getting him off the hook. But I do think that most of the other people who might have been running the joint would have made many of the same mistakes — and that some of them would not have been as willing to make as many big, scary bets on change as he has over the last few years.

And if you want to helpfully give Microsoft advice on what it should have done but didn’t — hey, it’s easy when you can do it retroactively — the road not taken seems obvious to me. The company would have been better off if it had spent less time defending and extending Windows’ turf, and more time acting like a company that wanted to kill off Windows with the next bright, shiny, useful thing. It should have assaulted its own monopoly with the same belligerent gusto it once applied to attacking Lotus and WordPerfect and Netscape. Ballmer didn’t do that when it would have made the most difference, and it’s awfully late in the game for his successor to try.

I think one thing missing here is the degree to which MS is loathed by a small cadre of elite and influential developers, who've spent the last two decades build open source, standards based, highly interoperable software. Walk through the development team of any silicon valley company, or any company for that matter that makes software no specifically targeted to Windows, and you'll find the majority, sometimes vast majority are developing software using Macs, and though that are using PC laptops are probably running Linux. MS' bullying, maxamalist winner take all approach to technology, not just its rival companies, but technologies it saw as anti-windows, were subject to campaigns of dis-information while new technologies and tools were rolled out to intentionally break compatibility and trap customers and developers in the MS Kingdom, new releases very often made their products worse as they were we many times filled with mis-features to extract the last possible dollar from their customers, and denied their competitors from even getting the leftover scraps. In these days of the patent wars, there's plenty bad behaviour of this sort to go around. But a great deal of what is touted as 'innovation' in technology is simply the result of not making intentionally inferior products that screw your customers, developers and everyone else in the industry.

Would we (the consumers) really be happy and thankful for being completely corralled in MS's realm ?

Would we really want to be beset from MS products in all of our nooks and crannies of our everydays life ?

I'm referring to an imaginative day like this : Your WP smartphone wakes you up. You check a few emails and skim over the news on your SurfaceRT/Pro, later be guided by Bing Maps through the traffic during your daily commute, in the office you turn on your Windows laptop and do all your daily chores and finally back home your switch on your Xbox for a gaming session ?

Microsoft held almost a monopoly on pcs, and their products were tailored for that particular market. Microsoft became a conservative company that failed to see the momentous changes in the computer and portable device markets. It totally underestimated the tablet and smartphone segments, perhaps because it didn't see how these devices could also affect the pc market. Windows lags behind,but it can still catch upIif it develops better products. A friend of mine bought a Windows 8 smartphone because he doesn't like android, so apparently there's room for Microsoft in the smartphone market. However, it should understand that the era of oligopoly is over andtthat it should begin to care more about what customers want and need.

Tried to read most of the replies, but didn't find a single suggestion of an alternative to Windows. Android ? Really ? Android is based on Linux and a lot of people ***LOVE*** Android ! But as someone who is typing this reply on a personally customized Linux disc, Android itself is fraught w/ similar tech issues as Windows. Moreover many years ago, when I mentioned on Linux discussion boards that Linux would be a viable alternative to Windows w/ a credible compatibility layer (Wine, Crossover Office, whatever), the hardcore Linuxen dismissed the idea the same way they dismiss it now. Hard-core Linuxen want Linux to be adopted purely on its own merits.

Once upon a time, there was a BeOS, some even imagined Sun's Solaris as a possible contender. If you don't recognize those names or even if you do, my point is made.

Regarding Mr Ballmer, the company is still profitable, it has an admirable stock price, has plenty of cash on hand (I'll it to serious financial-types to argue how desirable that is), and has never been saddled by debt. I'd personally LOVE to have Microsoft's problems...

The author's conclusion in the last paragraph is just plain stupid. It makes no sense to say that Microsoft should have attacked its premier product. I've never liked Microsoft products, and I'm not defending them, but the article is meaningless.

Microsoft made a mistake by preferring reverse compatibility over security (multi-user). Windows, until recently, and even that's debatable, is still a single user system. Windows could never distinguish between an administrator and a user. That is the reason there are so many viruses. This decision (a marketing decision to keep users on the platform) was shortsighted as users can have access to any computer because once a person logged in, the computer thought everything coming in was "okay". Which thanks to the internet connections, it was not. Microsoft did not want to force their users to buy new software/hardware, and the result was a long gap for the next generation of Windows after XP. Microsoft simply did not want to change it!

The decline of Microsoft (and it's probable continued decline) is not a Balmer problem although his shortsightedness contributes. It actually is and was a Gates problem (and still is). Don't believe me then answer two questions. Why has Microsoft never created a good set of tools to maintain their operating systems (which has given rise to a huge 3rd party industry)? Why was something as basic as anti-virus software not a product until recently (Microsoft Security Essentials)? Stumped? Don't be, it's simple. "Hey hon, this machine is getting slower and slower...maybe it's time we traded it in." And millions of you did exactly that when in fact ten year old machine technology is actually adequate for the vast majority of people that use the net today. So you catch on? Greed. Each new machine comes with Windows and MS makes money. There was and continues to be to this day no incentive to make an excellent product. A simple example is Docx...not being compatible with prior versions of word....hmm, and yet converters exist all over the net. What should MS have done? And why is it literally tragic? Simple...make a good product. Be innovative and make additional good products. They literally had the world by the tail. What instead was the focus........crushing competition, milking Windows, buying companies for their technology and not (as is part of Googles focus and almost all of Apples) looking to innovate. The tragedy, for anyone who has fought blue screens of death and more is MS wasted billions of our hours frustrating us and lost it's position while doing so. Today, despite continued product releases, the world is and has become aware. Examples...Unbunto and Linux are perfectly adequate and FREE. The number of people I know (and I know a lot of people) who actually use all the buttons and capability within MS Office (beyond Office 2003) I can count on one hand. Worse for MS....is there are many free Office suites that are more than adequate. So who could fix the problem...Gates curiously and not because he is the best leader on the block (but the perception is). How, again simple...take the company back to basics, get rid of the current culture (not easy) and spend some of those billions on innovating...the opportunities are endless. By the way, for those of you who believe Bill is a leader...watch the video of the earthquake when he was at the podium and what he did.....walk off the stage without a word to all those in panic...not my kind of guy. Case rested.

I've never bought into the Windows bashing that is so trendy among those who consider themselves the techie-elites, mainly because I've never had the problems I read about on forums frequented by the Windows bashers. I've used Windows since I started using a computer in 1994. The reason I chose Windows over the Apple product back then is because it was affordable (and perhaps, with prescience I didn't know I had, I didn't find paying for god-awful-looking yachts desirable). I've had almost twenty productive and enjoyable years using Windows, writing and editing more than two-dozen so far and building about a dozen websites using Windows-compatible software. If Windows had not been available at a price I could afford, none of that would have happened. So, thank you Windows-folks, you gave me the tools to have a successful career.

Good points. In addition I'd save Windows has become tired and tiresome. The UI is still not that great. Crashed still occur. It's a very non-intuitive OS. Good for gaming. Excel is great. For anything else I prefer others.

The victory of Microsoft was the victory of mediocrity. I say that as someone who has used Windows and then Mac. The Windows OS is an impossible tangle. Can't be fixed. Reminds me of the gradual awareness that the US has turned its "lone superpower" delusion into self-destruction. Hey, "our" government s like Windows -- an impossible tangle. A Gordian Knot, awaiting an Alexander.

There are some Windows apps that run well on Mac, these can be, one would hope, evolved going forward

At some point, Mac decides to let its OS run on any Intel-based PC, and it's all over. Mac needs to beef up its technical staff, there will be lots of problems.

Unfortunately, Windows Outlook isn't one of them. When we switched from MS to Mac, my husband chose to install Outlook for the Mac on his desktop. Since then he has lost every email in every folder on three separate occasions. They simply vanish. Apparently this is such a common problem that MS technical support has a scripted fix that it goes through to recover the missing files. On my own Macbook, I stuck with the delivered mail program and have never experienced a single problem.

Interesting. I switched from the Mac e-mail app to Outlook for Mac, included in Office for Mac, and after some troubles setting it up - nerdy things like adjusting ports and such -- there were postings on the Web that gave advice on this -- it functions well. Also had to purchase a piece of software to translate Mac contacts into a form that Outlook could use. I think that cost $30.

I still get error messages about errors that haven't occurred, but that's a small annoyance. I get update alerts from Office for Mac and update whenever they appear.

Can't really blame Ballmer for the company flatlining the past 13 years. When Ballmer took over in year 2000 the Dept of Justice (DOJ) had just cut a deal. In exchange for not having to admit to having a monopoly, Microsoft promised to be on it's best behavior for 11 years. So from 2000-2011, Microsoft was hamstrung a bit in what they could do as far as innovation went because they were on sort of a probation.

It's only been the last couple years that MS has had pretty much free reign to do what they want and not worry about the DOJ breathing down their neck.

Well, the US authorities should have dismantled this monopoly for very very long. Microsoft's product are very expensive and still full with errors and, the worst, they have been forcing users to behave like they decided Plus, I hate Colibri!

P.S. - The GREATEST POINT in the article is "Hindsight is 100% more accurate than Foresight", "Everyone's an Excellent Monday Morning Quarterback", "Wish I Knew Then What I Know Now"....if I thought long enough about it I could come up with ten more, but U get the point.....easy for you to bash someone for his past errors. We should have had you as CEO instead, right?????

Steve, if you are reading this contact me. It's not magic.....it's deducing what the computing world NEEDS but doesn't yet know they need and want...that's the KEY to making MS's future as bright as it once was.

If MSFT pulled out of consumer, since they already need to deal with Android and Apple clients, they'll be more successful only dealing with profitable segments and ditching unprofitable segments. Let Intel and ARM fight it out with weapons drawn, for the consumer business. (Along with Apple, ATT, T-Mobile, Verizon, etc., etc., etc,).....

Very good analysis. MSFT may need to pull out of consumer and concentrate of business software and hardware and Cloud Computing and Internet Servers. Become like an Oracle / Amazon crossbreed, only work with Enterprises, B-to-B, etc., forget Windows consumer, let everything consumer become Andriod or Apple.....

I'm pretty sure that after the whole turn of the century, he's pretty much the guy that kept it together no matter HOW bad it got...for all the misses, they certainly were spectacular and I still love them.

@MediaCastleX You're in the minority. People use Microsoft products because they have to, not because they want to. I had a Windows Laptop and Office in College because I had to, not because I wanted to. Apple's computers were too expensive and Linux is garbage. That really left only 1 choice. To have to sit there and wait for your operating system to update itself constantly is annoying. If Microsoft got it right the first time, they wouldn't need so many updates.

I have a new iMac and I've done exactly one OS update in the 7 months I have owned it. My Windows 7 computer, on the other hand, has had at least half dozen updates requiring lengthy reboots.

There's really nothing surprising about this at all for anyone who's been paying attention to Microsoft's slow-motion train wreck during the last two years of Windows 8/Windows RT/Metro UI/Surface/Apps Store/Xbox One. Flipping a penny would have yielded better decision making than Ballmer because a penny would have been right at least half the time.

The only surprising thing is that the magnitude of this disaster must be known internally to be so much greater than what is known externally that the board was actually finally forced to oust Ballmer.

Unfortunately, for Microsoft to have any chance at all of a prosperous long term future, Ballmer needs to leave immediately rather than a year from now. In today's extremely fast paced tech world, a year of aimless drifting for a company like Microsoft is practically an eternity in tech dog years. I mean, really, how much time has Microsoft got left? Microsoft is the only company in the world whose principal revenue stream comes from selling operating system software. In fact, it's essentially the ONLY company in the world selling operating system software. All other companies essentially give away the operating system software bundled with either services or hardware. One has to wonder how much longer Microsoft can survive based on such a singular model.

Very good critique! Microsoft is an operating system monopoly in the world of industry, trade and commerce. That was and remains their core business.

Microsoft was never and struggles with being a "consumer" driven company. Look at the cost of their apps! Apple has always been a consumer driven company. They now dominate because networked computing (anywhere anytime apps) are primarily consumer driven using integrated platforms for voice, text and internet, that "leave the office" and mostly for consumer demand.

Another example is Blackberry. It built a hardware and OS for business; never for the consumer. They should have stayed with it. Yes become another IBM. Businesses are not tech hungry or early adopters. They need systems that aid the production of wealth and not fashion, convenience or pleasure.

@AsokSmith What have you been smoking? Something really strong I guess. "Microsoft is the only company in the world whose principal revenue stream comes from selling operating system software."

Ever heard of Exchange Server? SQL Server? Visual Studio? Microsoft Office? Do you have ANY CLUE what these products do? NO, your mind is too out in left field from smoking whatever it is you're on......

I have Microsoft Windows 7. I do not have Exchange Server. I don't have SQL server. I don't use Visual Studio (I prefer Delphi). I won't have MS Office on my computer. (Libreoffice is all I need).

Do you detect the trend?

Look for the ground in which your little forest of trees is growing. A computer HAS to have an OS to run at all, let alone run any of that other crap. A computer DOES NOT HAVE TO HAVE ANY OF THAT OTHER CRAP in order to run. Microsoft made some money from me because they have an OS I use. The other stuff has much more competition and (arguably) other products that do the same thing are better, and Microsoft never made any money from me for any of it.

These are the basics of business. Supply what everyone NEEDS.

Yes, Microsoft does provide other software. It's expensive. It's not all that great. But none of it will work on a computer without an OS and none of it is NEEDED except the OS. That means Microsoft is primarily an OS company because that's the ONLY product they sell that EVERY computer needs. They forgot this in their rush to become the "next Apple". Apparently, you forgot, too.

Always keep focused on the basics. Microsoft didn't. Maybe now they'll get back to them.